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DOI: 10.1055/s-0029-1216982
Propargyl-Substituted Phosphonocarboxylates: Efficient Synthesis and Application to Click Chemistry
Publication History
Received
6 March 2009
Publication Date:
28 August 2009 (online)
Abstract
An efficient pathway for the selective preparation of monopropargyl-substituted phosphonocarboxylate (PC) has been developed via the addition of sodium acetylenide to ethylidenephosphonate. The reaction works perfectly on multi-gram scales. The synthesis of the corresponding methyl(propargyl)-, trifluoromethyl(propargyl)-, and dipropargyl-substituted derivatives was elaborated based on direct alkylation of either the correspondingly substituted phosphonocarboxylates or methylene phosphonocarboxylate with excess of propargyl bromide. A series of novel potentially biologically active 1,2,3-triazole-containing phosphono-carboxylates were synthesized using copper(I)-catalysed 1,3-dipolar cycloaddition of organic azides with propargyl-substituted phosphonocarboxylates.
Key words
phosphonocarboxylates - ethylidenephosphonate - alkylation - sodium acetylenide - 1,3-dipolar cycloaddition - azides - phosphorylated 1,2,3-triazoles
